


The Wanderer (Won't be Wanderin' No More)

by RightInTheOvaries



Category: Supernatural
Genre: Alternate Universe, Awkward Dean, But it's on purpose, Destiel - Freeform, M/M, Slightly OC Dean, Some Fluff, Some canon elements??, high scool au, human!Cas, hunter!dean, its cuz he has a crush, sassy!Sam
Language: English
Status: In-Progress
Published: 2015-06-07
Updated: 2015-06-07
Packaged: 2018-04-03 08:34:08
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,443
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4094194
Author URL: https://archiveofourown.org/users/RightInTheOvaries/pseuds/RightInTheOvaries
Summary: <blockquote class="userstuff">
              <p>Dean's earned himself the title "The Wanderer," and rightfully so. He has a strict love-em-and-leave-em attitude, and leaves a string of heart breaks wherever he goes. It's something he's proud of (and, let's be honest, it's a major stroke to his ego).</p><p>But of course, there wouldn't be much of a story if he didn't meet Castiel Novak, with the bright eyes and intense focus. Dean finds his iron grip on his title slipping the more he spends time with Castiel, and he's not quite sure if he should pursue what's clearly in front of him or hop back in his dad's car and forget the whole thing ever happened.</p><p>Based on the song "The Wanderer" by Dion. You should check it out to get a bit of background and why it applies so perfectly to Dean.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I know I shouldn't be starting a new story, but this one just popped into my head and I couldn't get it out! I have most of the story done, so I may just upload the whole thing today. We'll see.
> 
>  
> 
> But for now, enjoy!

He had become the boy fathers despised and mothers worried about. The boy with a reputation that could make Casanova jealous. The boy with a face and charm that made people fawn madly over him with just a single smirk and a well-timed wink.

Dean Winchester had become The Wanderer, and he loved it.

Despite his brother's slightly disapproving comments, Dean was not ashamed of his love-em-and-leave-em attitude- you could almost say he was proud of it. He grew wary of feelings and cocconed himself in the safety of quick fucks and the knowledge that he would most likely never see the people ever again to feel guilty about it, and Dean liked it that way. It had become routine.

When he stepped into Chemistry on October 17 in Somewhere, New Jersey, Dean immediately went to find the easier chicks (and possibly guys, he wasn't too picky) who would be perfect candidates to help boost his title a little more.

However, one glance at a boy with bright freakin' blue eyes had that plan soaring out the window without a second thought. Dean's eyes seemed glued to the other boy's intense ones, and it sort of felt like a staring contest.

"Mr. Winchester? Mr. Winchester!"

Dean visibly shook himself out of whatever trance he was trapped in, realizing someone was trying to get his attention. He turned to the teacher, whose name escaped him, and smiled sheepishly at her.

"Sorry," he muttered, straightening his posture.

"It's alright," she said. "Please, have a seat next to Haley, and don't make any trouble."

Haley raised her hand when Dean looked around the room quizzically. The tables were round and had at least four people sitting at each one. Dean grinned wolfishly when he noticed that the table he was directed to was occupied by three girls, including Haley. They all giggled when he lerred at them, but we're silenced quickly when the teacher shot them a threatening glare.

"I dont know what you were taught at your other school, Dean, but we'll worry about that later. For now, please just try to catch on. Today..."

Dean tuned her out, staring at the side of a brunette's face (Jolie, she had whispered to him) dazedly. The problem with changing schools like he changed his socks was that it was hard to really "catch on" to anything he was being taught. He gave up pretty soon after he figured that out, and Dean was pretty content with just zoning out in classes, especially ones he didn't like.

It wasn't until he felt something sharp poking him in the shoulder did Dean realize the class was shifting around. Dean looked up to see Haley, her finger outstretched with a long claw pressed onto the nail. She giggled before sliding into the seat next to Jolie, and Dean understood everyone was partnering up. Another thing that sucked about constantly being the new kid was that could he never had friends in the class to partner up with.

Dean searched the room for anyone sitting by themselves and found blue eyes staring unabashedly at him. The boy gestured for Dean to join him at the empry table he was seated at, and Dean nodded gratefully before standing up.

"Thanks, man," Dean said as he plopped himself down. 

"No problem, Dean," the boy replied. "I'm Castiel."

He stuck out his hand to be shook, which, okay, odd, but Dean thought the weird gesture went with the weird name. He stiffly shook the hand, very carefully not paying attention to how smooth and warm it felt against his own.

"Castiel?" Dean chuckled. "That's unique."

Castiel natroed his eyes. "If you have any kind of problem-"

"Whoa, whoa, easy dude; nobody said anything about having a problem," Dean tried to pacify. "I was just saying your name probably isn't going win the Most Popular Name of the Year award any time soon."

Castiel blinked. "My apologies; I'm just used to being picked on because of my name."

Dean struggled to find an answer because, honestly, how the Hell do you reply to that? Luckily, Castiel saved him from having to speak by talking again.

"Where would you wish to start, Dean?" he asked, attention directed solely on Dean.

Dean squirmed a bit under the gaze, but met it head on. "I'm gonna be honest and say I didnt pay attention, like, at all. I don't even know what we're supposed to be doing.

"No worries," Castiel told him while opening his textbook. "It's simple, really."

Dean actually listened to Castiel explained the activity, and even found himself understanding the topic. Together they solved equation after equation with ease (something that shocked Dean himself), finishing a full ten minutes before the bell was supposed to ring.

"Dude, you're awesome at this stuff! How come you're not in Honors or something?"

Castiel blushed faintly. "I just transferred in a few weeks ago, so I was placed in all regular classes. It's a good thing, though. I haven't had to the time to make any friends, let alone catch up on all the work they've given me."

"Still, dude," Dean said, then thought of something Castiel said. "Say, it looks like we're in the same boat: you and I have yet to make friends. Wanna have lunch together?"

Dean was nothing if not direct, but his forwardness surprised him a little. But the offer was out there, and Dean was sort of happy he blurted it out. It would suck majorly if he had to spend lunch by himself.

Castiel very briefly thought it over. "Alright."

"Really?"

"Why would I lie?"

They chattered for the remaining time left in Chemistry, mostly about their schedules and the few teachers Dean had met so far. He found himself a little disappointed when he found out he only had the one class with Castiel, which surprised him. He'd only met the dude a literal half an hour before, but Dean was already growing attached to the boy (and he didn't want to think of the repercussions that would lead to, so he didn't).

The bell rang, jolting the both of him. They agreed on a meeting place before gathering their items hastily.

"Goodbye, Dean," Castiel parted with.

"See ya later, Cas," Dean said, the nickname coming easily.

****

Lunchtime approached quickly enough, but that could have been because Dean slept through the remaining block before it. He found the cafeteria easily by following the flow of students, and soon found himself ordering a slice of pizza with a can of Coke. However, once he paid, Dean found he had no clue where he was going and began to silently panic. He didn't establish a specific table to sit at with Cas, didn't even know if Cas remembered the plan-

"Hey, Dean," a high-pitched voice greeted. 

"Oh," Dean composed himself, turning to see-what's her name? "Haley, right? Hey."

She giggled and blushed pink. "I was just wondering if you wanted to sit with me and a few friends."

Dean was tempted, but, "Sorry, I already promised someone I'd eat with them today."

Thankfully, Haley appeared to have understood and nodded. "No problem. Just know that the offer doesn't expire."

With a wink, she walked away to where a few other hot chicks were seated. Once more, Dean felt the urge to forget about Cas and go slide up next to Haley, maybe get her number. But Dean, for some reason, felt as if he would be betraying his new possible friend, so instead he started searching the cafeteria for him.

Lucky for him, Cas wasn't as difficult to spot as he worried. The tables were packed to the brim with upper and lower classmen alike, but somehow the blue eyed boy managed to find a secluded end of one. Dean grinned when he plopped his tray down loudly, startling Castiel from his (friggin' thick) novel.

"Hello, Dean," he greeted quietly. "I was beginning to think you forgot about our arrangement."

Dean didn't know why, but that sort of hurt. Still, he brightened his smile and sat down.

"'Course not," he said. "Who could forget about someone like you?"

Which, okay, what? Dean clamped his mouth shut hastily, realizing how flirtatious that sounded. He hoped Cas didn't notice, but the red that bloomed from his cheeks may have said otherwise.

"Um," Dean cleared his throat, "did you already eat?"

There was nothing in front of Cas that signaled he had eaten anything. There was simply the huge book (Les Miserables, what the hell?) on the table.

"No," Castiel answered. "I, uh, forgot my money. It's alright though, I'm not hungry."

Dean's widened. "Shit, man, all you had to do was ask. Here, take a few bucks and get yourself some fries or something, jeez."

Cas shook his head vigorously. "Dean, I couldn't. It's your money-"

"Nah, don't worry about it. Think of it as me paying you back for helping me in Chem before."

Cas still looked hesitant to accept the proffered bills, so Dean grabbed one of his hands-and did not think about how warm and smooth it was, thank you very much-and dropped the money in it. Realizing he lost the battle, Cas sighed and stood up, closing his palm.

"Watch my book for me, please," he instructed.

"Of course," Dean replied.

The line had dwindled significantly since Dean had waited on it, so Cas was back within ten minutes. During that time, Dean tried to find the most attractive girls around him, but he couldn't find the motivation to do so. He thought that extremely strange, but Cas returned so he didn't have much time to dwell on it.

"Eat quickly, dude, we only got like fifteen more minutes."

Together, they munched in companiable silence, occasionally breaking the peace for a quick conversation. Dean complained about the unfair essay assigned to him in English and listened when Cas spoke eagerly about some bee farm he visited a week before. Dean caught himself finding it endearing, but didn't allow himself to freak out over it.

When the bell shrieked, the two of them jumped a mile high. They laughed at each other's terrified expressions before gathering their trash and throwing it away. Dean commented on the size of Cas's book, but Cas defended himself in saying the plot was worth the length. When they passed through the door and found out they were going in different directions, they both paused.

Castiel must have noticed Dean's struggle in getting any words out (and when did he start having trouble talking to anyone), because he asked, "Same time tomorrow?"

Dean had to swallow several times before he responded, but then remembered something and chuckled. "Tomorrow's Saturday, Cas. But Monday, yeah, sign me up."

Cas offered a blinding smile, and Dean found himself locked in another intense stare off. He could have stayed there for months, years, who knew? but the second bell rang, signaling their tardiness.

"Shit," Cas swore, mildly surprising Dean. "I look forward to Monday, Dean."

"Bye, Cas," Dean said, a grin blooming at the other boy's words.

If he continued through the rest of the day with the same gooey smile on his face, well, that was no one's business but his own.


	2. Chapter 2

**Summary for the Chapter:**

> This is where our boy Dean gets a little awkward.

It wasn't until the last bell rang did Dean realize he had not talked to his younger brother the entire school day. Usually, he sought him out during lunch or in the halls at least once to make sure he was okay. He didn't know what to feel once he realized it was because he was too distracted with Cas.

Dean felt utterly relieved when he saw Sam walk out to meet him near the flagpole in front of the school, where they agreed to find each other that morning. He quickly scanned him to make sure there were no blatant injuries, a ritual he repeated every time he saw his brother.

"Hey, Sammy," he grinned, pushing his weight off the pole. "How was your first day?"

"I feel like I'm asked that more times in a year than the average kid is in his life," Sam grumbled, falling into step with Dean.

"Ah, but Sammy, we are not anywhere close to average kids," Dean said with a bit of glee.

He heard Sam mumble to himself, things along the lines of "don't I know it" and "quit calling me Sammy." The rest of the walk was quiet, but the motel they checked into a few days previous wasn't too far from the school. Dean enjoyed the silence, for it allowed him to look around and try to memorize any spectacular details about the town, but there were none to be found. Just like almost every other place they temporarily settled into, it was lacked personality.

"Dude, if you're looking for inspiration, I hear Honolulu's beautiful this time of year," Sam commented, making Dean realize he spoke out loud. "Want me to print out some pictures and add 'em to the book?"

Dean had been given a scrap-booking assignment a dozen schools back, but, of course, he didn't bother with it because the Winchesters were back on the road the next day. Sam had seen it before Dean could throw it away, and ever since the two had been filling it with pages upon pages of places they would like to visit after they retired from hunting. (Dean decided not to mention that hunting wasn't exactly something you could retire from because his brother looked so damn pleased with the idea.)

"Sounds good, shorty," Dean replied, ruffling Sam's shaggy hair.

Sam groaned, ducking away. "Just you wait; one day I'll be so much taller than you."

"Yeah, like that'll happen."

****

Dean expected that weekend to pass like pretty much every other weekend he experienced: on his ass watching whatever was on TV. However, while that part was true, he also found himself sort of anxious, as if he couldn't stand the wait for something. This Dean found strange because there was nothing to really wait for except school on Monday. But then Dean remembered the deal made with Castiel and a thousand butterflies shot around in his stomach, a rare feeling for him.

"What's got you all smiley?" Sam asked from Dean's right side on the couch.

"Huh?"

"I don't know, man, your face just lit up like crazy," Sam shrugged before a mischievous smirk spread across his face. "Who is she?" 

Dean's brow creased in confusion. "Who is who?

"Dude, you're so crushing on a chick," Sam said excitedly. "That look right there is the look of love."

"Shut up, Sam, I ain't crushing on no chick," Dean snapped with a devilish grin. "I got a total hard-on for one. There's a difference."

"Gross, Dean, you didn't have to share that," Sam whined, sliding off the couch. "I'm gonna go finish my homework and pretend this conversation didn't happen."

Unlucky for Sam, sharing a hotel room meant there was basically no privacy. Dean followed him to the small table, giving lewd comments the entire way.

"Man, you shoulda seen her," he chuckled. "Dark hair perfect for pulling when she goes down, and don't even get me started on those lips-"

He was cut off by a well-aimed pillow soaring into his head. Dean laughed and half-heartedly tossed the pillow back onto the bed it came from, enjoying the way Sam's face turned more and more red each second.

"You didn't even let me get describe the blue jewels she has for eyes, the way the just pull you in-"

"I don't wanna know, you jerk," Sam yelled, covering his ears.

"Have it your way, bitch," Dean responded lightly.

He walked into the bathroom, where he had a ten minute freak out because he basically just described Cas to Sam. Dean probably had a crush on the one actual friend he made in months, hell, years, after just one day of knowing him. It all sounded so fucking middle-schoolish he would have laughed if it weren't for the way he was panicking.

Fuck, he was so screwed.

****

"Good morning, Dean," Cas said from behind him.

Dean jumped fucking ten feet in the air he was so startled. "Oh, um, hey, h-hi Cas. We're gonna need to get you a bell or something, man, you scared the hell outta me."

"My apologies," Castiel said.

Damn, he looked so earnest Dean thought it was adorable. Fuck feelings, fuck his fucking life.

"D-don't worry about," Dean stuttered, cursing himself for being such an idiot. "There are no worries here, abosolutely none at all."

Dean snapped his jaw shut to prevent himself from making himself look even more stupid. There was nothing much to say beyond that anyway, so the two boys were content to just, well, stare at each other. Dean was surprised that he was already so comfortable about it. What did he tell Sam? "Blue jewels." Could he be anymore girlish?

The bell rung, which meant class was starting. Cas rushed back to his seat while the teacher walked into the room. Dean couldn't help but watch him as he left, and it took actual effort to rip his gaze from Cas to the teacher. Not that that helped, honestly, because Dean's thoughts somehow always drifted back to him. He didn't even notice someone calling his name, he was so deep in thought.

"Dean!" He was shook once, twice. "De-e-e-an?"

"Cas," Dean murmured before nodding his head to focus. "Crap, Cas, sorry. I didn't realize you were trying to get my attention."

"I didn't notice," Cas said sarcastically, and fuck, that little smirk did things to Dean that made him feel hot and sticky. "Are we still on for lunch?"

"Yeah, yeah, totally," Dean stumbled, face pink. "We are so on for that lunch. Um, when is lunch?"

Cas's smirk only grew. "One more block. Speaking of blocks, the next one starts in one minute forty eight seconds, so I suggest you get a move on. Forty three, forty two..."

Dean whipped his head around, only just finding out that they were the only two in the room. Even Mrs. Whatshername was gone.

"Shit, thanks," Dean rushed out. "I'll catch up with you later."

Somehow Dean knew that the smug look on Cas's face deepened, so he ran out of the room in a hot second before he could find out what the dark look would do to his already quite pressing arousal.

****

"Hello, Dean," Castiel greeted with an upbeat tone.

This time it was he who found Dean in the cafeteria and not the other way around. Dean was already halfway through a burger and very convinced Cas wasn't coming by that point, so seeing him was an immense relief. Dean didn't even want to think about what that meant, so he pushed it aside.

"I hope you'll forgive my tardiness, but I had to meet with one of my teachers. We had a lengthy arguement before he gave me the extra seven points I deserved on an essay."

"Is that what's gotcha so perky?" Dean laughed, offering his fries.

Castiel blushed. "I'm sorry."

"No need to be sorry, dude, you have a right to be happy. It's a damn good look on you."

Their wide eyes met each other across the table. Dean sputtered while Cas merely acknowledged his actions.

"I mean in a completely, you know, platonic way. Like, no homo or anything."

Cas snorted at Dean's choice of words. He could have sworn Cas was going to say something else, but before he could get anything else the shrill bell resounded in the cafeteria. Dean, embarrassed beyond belief, stood up quick as lightning and went to dump his plate into the nearest trashcan. He stuffed his hands in his jeans' pockets and bowed his head, desperate to just get out of the room, but a strong hand on his bicep stopped him.

"Dean, wait," Castiel said. "Wait, here's my number. Text me or call me or... something."

Dean nodded dumbly, taking the slip of paper with Cas's near handwriting. He was at loss for words, couldn't get beyond the fact that Cas wanted to talk to him outside of school. Was he interested too? Is that was this meant?

Dean reigned his thoughts in before he could ponder that any further. Instead, he flashed Cas a warm smile and pocketed the paper.

"Thanks, Cas, I will," Dean said. "Um, I mean, I'll text you or call you or... something."

They shared bashful grins before parting. Once more, Dean had a dopey smile plastered on his face and it was all because of Cas.

**Author's Note:**

> Please leave a comment to tell me what I can improve upon, and if you liked it, don't be shy! Press that button and give this story a kudos.


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